CA2563017C - Substituted cyclohexylacetic acid derivatives - Google Patents

Info

Publication number

CA2563017C

CA2563017C CA2563017A CA2563017A CA2563017C CA 2563017 C CA2563017 C CA 2563017C CA 2563017 A CA2563017 A CA 2563017A CA 2563017 A CA2563017 A CA 2563017A CA 2563017 C CA2563017 C CA 2563017C

Authority

CA

Canada

Prior art keywords

dimethylamino

hydrochloride

acetamide

phenyl

mixture

Prior art date

2004-05-10

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical class OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 title claims description 62
• 150000001875 compounds Chemical class 0.000 claims abstract description 67
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 41
• 239000003814 drug Substances 0.000 claims abstract description 35
• 208000002193 Pain Diseases 0.000 claims abstract description 34
• 230000036407 pain Effects 0.000 claims abstract description 21
• 230000003444 anaesthetic effect Effects 0.000 claims abstract description 13
• 229940005483 opioid analgesics Drugs 0.000 claims abstract description 13
• 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims abstract description 12
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 10
• 230000001771 impaired effect Effects 0.000 claims abstract description 10
• 230000001777 nootropic effect Effects 0.000 claims abstract description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 9
• 230000000694 effects Effects 0.000 claims abstract description 9
• 208000000094 Chronic Pain Diseases 0.000 claims abstract description 7
• 206010012335 Dependence Diseases 0.000 claims abstract description 7
• 208000004880 Polyuria Diseases 0.000 claims abstract description 7
• 238000011260 co-administration Methods 0.000 claims abstract description 7
• 230000035619 diuresis Effects 0.000 claims abstract description 7
• 229940079593 drug Drugs 0.000 claims abstract description 7
• 230000004770 neurodegeneration Effects 0.000 claims abstract description 7
• 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 7
• 239000002858 neurotransmitter agent Substances 0.000 claims abstract description 7
• 230000028327 secretion Effects 0.000 claims abstract description 7
• 208000009132 Catalepsy Diseases 0.000 claims abstract description 6
• 206010012735 Diarrhoea Diseases 0.000 claims abstract description 6
• 206010046543 Urinary incontinence Diseases 0.000 claims abstract description 6
• 206010047853 Waxy flexibility Diseases 0.000 claims abstract description 6
• 230000001154 acute effect Effects 0.000 claims abstract description 6
• 208000005298 acute pain Diseases 0.000 claims abstract description 6
• 208000022531 anorexia Diseases 0.000 claims abstract description 6
• 230000002082 anti-convulsion Effects 0.000 claims abstract description 6
• 206010061428 decreased appetite Diseases 0.000 claims abstract description 6
• 206010015037 epilepsy Diseases 0.000 claims abstract description 6
• 230000037406 food intake Effects 0.000 claims abstract description 6
• 235000012631 food intake Nutrition 0.000 claims abstract description 6
• 230000008991 intestinal motility Effects 0.000 claims abstract description 6
• 230000033001 locomotion Effects 0.000 claims abstract description 6
• 239000003158 myorelaxant agent Substances 0.000 claims abstract description 6
• 208000004296 neuralgia Diseases 0.000 claims abstract description 6
• 230000002981 neuropathic effect Effects 0.000 claims abstract description 6
• 208000021722 neuropathic pain Diseases 0.000 claims abstract description 6
• 239000000014 opioid analgesic Substances 0.000 claims abstract description 6
• 208000019901 Anxiety disease Diseases 0.000 claims abstract description 5
• 206010006895 Cachexia Diseases 0.000 claims abstract description 5
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 5
• 206010020772 Hypertension Diseases 0.000 claims abstract description 5
• 208000001953 Hypotension Diseases 0.000 claims abstract description 5
• 208000020358 Learning disease Diseases 0.000 claims abstract description 5
• 208000026139 Memory disease Diseases 0.000 claims abstract description 5
• 208000019695 Migraine disease Diseases 0.000 claims abstract description 5
• 208000008589 Obesity Diseases 0.000 claims abstract description 5
• 208000003251 Pruritus Diseases 0.000 claims abstract description 5
• 206010039966 Senile dementia Diseases 0.000 claims abstract description 5
• 201000001880 Sexual dysfunction Diseases 0.000 claims abstract description 5
• 208000009205 Tinnitus Diseases 0.000 claims abstract description 5
• 208000010877 cognitive disease Diseases 0.000 claims abstract description 5
• 230000002950 deficient Effects 0.000 claims abstract description 5
• 208000035475 disorder Diseases 0.000 claims abstract description 5
• 230000036543 hypotension Effects 0.000 claims abstract description 5
• 201000003723 learning disability Diseases 0.000 claims abstract description 5
• 230000003137 locomotive effect Effects 0.000 claims abstract description 5
• 206010027599 migraine Diseases 0.000 claims abstract description 5
• 235000020824 obesity Nutrition 0.000 claims abstract description 5
• 231100000872 sexual dysfunction Toxicity 0.000 claims abstract description 5
• 208000011580 syndromic disease Diseases 0.000 claims abstract description 5
• 231100000886 tinnitus Toxicity 0.000 claims abstract description 5
• 230000009278 visceral effect Effects 0.000 claims abstract description 5
• 208000009935 visceral pain Diseases 0.000 claims abstract description 5
• 208000007848 Alcoholism Diseases 0.000 claims abstract 4
• 206010013654 Drug abuse Diseases 0.000 claims abstract 4
• 206010001584 alcohol abuse Diseases 0.000 claims abstract 4
• 208000025746 alcohol use disease Diseases 0.000 claims abstract 4
• 201000009032 substance abuse Diseases 0.000 claims abstract 4
• 208000011117 substance-related disease Diseases 0.000 claims abstract 4
• -1 benzodioxolanyl Chemical group 0.000 claims description 275
• 239000000203 mixture Substances 0.000 claims description 209
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 102
• 150000003839 salts Chemical class 0.000 claims description 50
• 239000002585 base Substances 0.000 claims description 49
• 229920006395 saturated elastomer Polymers 0.000 claims description 38
• 238000000034 method Methods 0.000 claims description 32
• 125000003118 aryl group Chemical group 0.000 claims description 28
• 230000008569 process Effects 0.000 claims description 22
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 21
• 238000002360 preparation method Methods 0.000 claims description 21
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 19
• 239000003054 catalyst Substances 0.000 claims description 19
• 125000001072 heteroaryl group Chemical group 0.000 claims description 19
• 125000004076 pyridyl group Chemical group 0.000 claims description 19
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 18
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 16
• 125000001544 thienyl group Chemical group 0.000 claims description 16
• 239000002253 acid Substances 0.000 claims description 15
• 125000001624 naphthyl group Chemical group 0.000 claims description 15
• 125000002541 furyl group Chemical group 0.000 claims description 14
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 13
• XUYJLQHKOGNDPB-UHFFFAOYSA-N carboxymethyl phosphonic acid Natural products OC(=O)CP(O)(O)=O XUYJLQHKOGNDPB-UHFFFAOYSA-N 0.000 claims description 13
• 125000001041 indolyl group Chemical group 0.000 claims description 13
• 239000000126 substance Substances 0.000 claims description 13
• 239000003153 chemical reaction reagent Substances 0.000 claims description 12
• 150000002148 esters Chemical class 0.000 claims description 12
• 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 11
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 11
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 11
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 10
• 150000001768 cations Chemical class 0.000 claims description 10
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 9
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 9
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 9
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 8
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 7
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 7
• 125000000217 alkyl group Chemical group 0.000 claims description 7
• 150000001412 amines Chemical class 0.000 claims description 7
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 150000003254 radicals Chemical class 0.000 claims description 7
• 230000009467 reduction Effects 0.000 claims description 7
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 6
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 6
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 6
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 6
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 6
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 6
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 6
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 6
• 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 6
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 6
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 6
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 6
• CJYQKUZVHJLIGS-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexylidene]-n-[2-(1h-indol-3-yl)ethyl]acetamide;hydrochloride Chemical compound Cl.C1CC(=CC(=O)NCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC(F)=C1 CJYQKUZVHJLIGS-UHFFFAOYSA-N 0.000 claims description 5
• QQPIWEXJHHUYSU-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(4-fluorophenyl)cyclohexylidene]-n-(3-phenylpropyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC(F)=CC=2)CCC1=CC(=O)NCCCC1=CC=CC=C1 QQPIWEXJHHUYSU-UHFFFAOYSA-N 0.000 claims description 5
• ZUTROUQLHSKEOI-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(4-fluorophenyl)cyclohexylidene]-n-[2-(1h-indol-3-yl)ethyl]acetamide;hydrochloride Chemical compound Cl.C1CC(=CC(=O)NCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=C(F)C=C1 ZUTROUQLHSKEOI-UHFFFAOYSA-N 0.000 claims description 5
• IQFHGPWESACTJS-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-[3-(1h-indol-3-yl)propyl]acetamide;hydrochloride Chemical compound Cl.C1CC(=CC(=O)NCCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 IQFHGPWESACTJS-UHFFFAOYSA-N 0.000 claims description 5
• XVNCJNDEVIOODN-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-[5-(1h-indol-3-yl)pentyl]acetamide;hydrochloride Chemical compound Cl.C1CC(=CC(=O)NCCCCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 XVNCJNDEVIOODN-UHFFFAOYSA-N 0.000 claims description 5
• 150000005840 aryl radicals Chemical group 0.000 claims description 5
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
• XFTPQJQBMJHZKF-UHFFFAOYSA-N methyl 2-[[2-[4-(dimethylamino)-4-phenylcyclohexylidene]acetyl]amino]-3-(1h-indol-3-yl)propanoate;hydrochloride Chemical compound Cl.C=1NC2=CC=CC=C2C=1CC(C(=O)OC)NC(=O)C=C(CC1)CCC1(N(C)C)C1=CC=CC=C1 XFTPQJQBMJHZKF-UHFFFAOYSA-N 0.000 claims description 5
• BBPOBTJKFXYUSK-UHFFFAOYSA-N n-benzyl-2-[4-(dimethylamino)-4-phenylcyclohexylidene]acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1=CC(=O)NCC1=CC=CC=C1 BBPOBTJKFXYUSK-UHFFFAOYSA-N 0.000 claims description 5
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 5
• 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 4
• JOKLEJREDCNIKD-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexyl]-n-[1-(1h-indol-3-yl)propan-2-yl]acetamide;hydrochloride Chemical compound Cl.C=1NC2=CC=CC=C2C=1CC(C)NC(=O)CC(CC1)CCC1(N(C)C)C1=CC=CC(F)=C1 JOKLEJREDCNIKD-UHFFFAOYSA-N 0.000 claims description 4
• RXQWCUNKUKVDHD-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexylidene]-n-(3-phenylpropyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=C(F)C=CC=2)CCC1=CC(=O)NCCCC1=CC=CC=C1 RXQWCUNKUKVDHD-UHFFFAOYSA-N 0.000 claims description 4
• FCWZPJHDDUOKHF-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexylidene]-n-[1-(1h-indol-3-yl)propan-2-yl]acetamide Chemical compound C=1NC2=CC=CC=C2C=1CC(C)NC(=O)C=C(CC1)CCC1(N(C)C)C1=CC=CC(F)=C1 FCWZPJHDDUOKHF-UHFFFAOYSA-N 0.000 claims description 4
• VIFMOYOHMQLGAS-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-(2-phenylethyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1CC(=O)NCCC1=CC=CC=C1 VIFMOYOHMQLGAS-UHFFFAOYSA-N 0.000 claims description 4
• VOQSWHYBHNXFFU-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-(4-phenylbutyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1CC(=O)NCCCCC1=CC=CC=C1 VOQSWHYBHNXFFU-UHFFFAOYSA-N 0.000 claims description 4
• CUJYIQNNCFPCIE-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-[2-(1h-indol-3-yl)ethyl]acetamide;hydrochloride Chemical compound Cl.C1CC(CC(=O)NCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 CUJYIQNNCFPCIE-UHFFFAOYSA-N 0.000 claims description 4
• YLKSRBBBJYTVKJ-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-[3-(1h-indol-3-yl)propyl]acetamide;hydrochloride Chemical compound Cl.C1CC(CC(=O)NCCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 YLKSRBBBJYTVKJ-UHFFFAOYSA-N 0.000 claims description 4
• XKTKPRVXGIGROW-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-[4-(1h-indol-3-yl)butyl]acetamide;hydrochloride Chemical compound Cl.C1CC(CC(=O)NCCCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 XKTKPRVXGIGROW-UHFFFAOYSA-N 0.000 claims description 4
• LULRVVPEJPXSTK-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-[5-(1h-indol-3-yl)pentyl]acetamide;hydrochloride Chemical compound Cl.C1CC(CC(=O)NCCCCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 LULRVVPEJPXSTK-UHFFFAOYSA-N 0.000 claims description 4
• BRQVUJAVGATRDQ-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-(1h-indol-3-ylmethyl)acetamide;hydrochloride Chemical compound Cl.C1CC(=CC(=O)NCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 BRQVUJAVGATRDQ-UHFFFAOYSA-N 0.000 claims description 4
• PLHMGPYQBIEXPI-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-(2-phenylethyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1=CC(=O)NCCC1=CC=CC=C1 PLHMGPYQBIEXPI-UHFFFAOYSA-N 0.000 claims description 4
• SVHZXTOUDQHWIH-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-(3-phenylpropyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1=CC(=O)NCCCC1=CC=CC=C1 SVHZXTOUDQHWIH-UHFFFAOYSA-N 0.000 claims description 4
• RTBXXECSCDIAOA-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-(4-phenylbutyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1=CC(=O)NCCCCC1=CC=CC=C1 RTBXXECSCDIAOA-UHFFFAOYSA-N 0.000 claims description 4
• GDICGRWNXYWJSE-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-[(4-fluorophenyl)methyl]acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1=CC(=O)NCC1=CC=C(F)C=C1 GDICGRWNXYWJSE-UHFFFAOYSA-N 0.000 claims description 4
• DASCBEIQPSWVQR-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-[2-(4-fluorophenyl)ethyl]acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1=CC(=O)NCCC1=CC=C(F)C=C1 DASCBEIQPSWVQR-UHFFFAOYSA-N 0.000 claims description 4
• NSDOZTVPWBRTLG-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-[4-(1h-indol-3-yl)butyl]acetamide;hydrochloride Chemical compound Cl.C1CC(=CC(=O)NCCCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 NSDOZTVPWBRTLG-UHFFFAOYSA-N 0.000 claims description 4
• JMILVWBBDLLQBD-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-[6-(1h-indol-3-yl)hexyl]acetamide;hydrochloride Chemical compound Cl.C1CC(=CC(=O)NCCCCCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 JMILVWBBDLLQBD-UHFFFAOYSA-N 0.000 claims description 4
• LWCOSZMDBZTTMB-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-pyridin-2-ylcyclohexylidene]-n-(3-phenylpropyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2N=CC=CC=2)CCC1=CC(=O)NCCCC1=CC=CC=C1 LWCOSZMDBZTTMB-UHFFFAOYSA-N 0.000 claims description 4
• VOYLFEWMTNNWFF-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-pyridin-2-ylcyclohexylidene]-n-[2-(1h-indol-3-yl)ethyl]acetamide;hydrochloride Chemical compound Cl.C1CC(=CC(=O)NCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=N1 VOYLFEWMTNNWFF-UHFFFAOYSA-N 0.000 claims description 4
• 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 4
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 4
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
• 150000001718 carbodiimides Chemical group 0.000 claims description 4
• 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
• 229910052763 palladium Inorganic materials 0.000 claims description 4
• 229910052697 platinum Inorganic materials 0.000 claims description 4
• 229910052703 rhodium Inorganic materials 0.000 claims description 4
• 239000010948 rhodium Substances 0.000 claims description 4
• MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 4
• QRLCIWHWUJFNRB-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(4-fluorophenyl)cyclohexyl]-n-(3-phenylpropyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC(F)=CC=2)CCC1CC(=O)NCCCC1=CC=CC=C1 QRLCIWHWUJFNRB-UHFFFAOYSA-N 0.000 claims description 3
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